4-(pyridin-4-yl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile | 109619-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(pyridin-4-yl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 4-pyridin-4-yl-2-sulfanylidene-5,6,7,8-tetrahydro-1H-quinoline-3-carbonitrile
• CAS: 109619-38-7
• 化学式: C₁₅H₁₃N₃S
• 分子量: 267.354
• InChiKey: RDDCJKWXCSJOSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(pyridin-4-yl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile 在 氢氧化钾 、 氨 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 4-Pyridin-4-yl-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  A Total Synthesis of a New Class of Biazine Thioglycosides

  摘要：

  A new method for the synthesis of bipyridinyl S-glycosides 11 and 12 has provided the title compounds in a higher yield. Application of a one-pot glycosylation methodology resulted in an efficient, high-yield synthesis of biazine S-glycosides 17-20 An X-ray diffraction analysis of 11 disclosed the conformation of this glycoside as the S-glycoside and not the corresponding N-form.

  DOI：

  10.1081/car-200045262
• 作为产物：
  描述：

  4-吡啶甲醛 在 吗啉 作用下， 以 乙醇 为溶剂， 生成 4-(pyridin-4-yl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Sharanin, Yu. A.; Shestopalov, A. M.; Litvinov, V. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1762 - 1770

  摘要：

  DOI：

文献信息

• Synthesis and domino reactions of polymethylene‐3‐cyanopyridine‐2(1 <i>Н</i> )‐thiones
  作者：Anatoliy M. Shestopalov、Lyudmila A. Rodinovskaya、Andrey A. Zubarev、Vladimir N. Nesterov、Bogdan I. Ugrak、Tatyana Ya. Dutova

  DOI：10.1002/jhet.3836

  日期：2020.2

  4‐chloroacetoacetic ester were introduced into the domino SN2 → Thorpe‐Ziegler → Guareschi‐Thorpe reaction to synthesize tetracyclic dipyridothiophenes. Starting from these compounds, 8,9‐polymethylenepyranothienodipyridines were also synthesized by the domino Knoevenagel → Michael → hetero‐Thorpe‐Ziegler reaction. Furthermore, a method for the synthesis of thienodipyridine annulated to the steroid skeleton

  一种新的和容易的三组分方法用于合成聚-3-氰基吡啶-2（1的展开Н由多米诺Knoevenagel反应→迈克尔从环烷酮，氰基硫代，和polymethoxy取代苯甲醛→heterocyclization→脱氢反应）-thiones。发现最后的脱氢步骤涉及亚芳基氰基硫代乙酰胺。将所得吡啶硫酮和4-氯乙酰乙酸酯引入多米诺S N中2→Thorpe-Ziegler→Guareschi-Thorpe反应合成四环二吡啶并噻吩。从这些化合物开始，还通过多米诺Knoevenagel→迈克尔→异索普-齐格勒反应合成了8,9-聚亚甲基吡喃并二吡啶。此外，提出了一种合成甾族化合物环化的噻吩并吡啶的方法。
• Single stage synthesis of 2-alkylthio(seleno)-4-hetaryl-3-cyano-5,6,7,8-tetrahydroquinolines
  作者：V. D. Dyachenko、V. P. Litvinov

  DOI：10.1007/bf02290871

  日期：1997.10
• 3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells
  作者：Chatchakorn Eurtivong、Victor Semenov、Marina Semenova、Leonid Konyushkin、Olga Atamanenko、Jóhannes Reynisson、Alex Kiselyov

  DOI：10.1016/j.bmc.2016.11.041

  日期：2017.1

  A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1-5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI(50) of 50-250 nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket. (C) 2016 Elsevier Ltd. All rights reserved.
• SHARANIN YU. A.; SHESTOPALOV A. M.; LITVINOV V. P.; MORTIKOV V. YU.; RODI+, ZH. ORGAN. XIMII, 22,(1986) N 9, 1962-1971
  作者：SHARANIN YU. A.、 SHESTOPALOV A. M.、 LITVINOV V. P.、 MORTIKOV V. YU.、 RODI+

  DOI：——

  日期：——
• Sharanin, Yu. A.; Shestopalov, A. M.; Litvinov, V. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1762 - 1770
  作者：Sharanin, Yu. A.、Shestopalov, A. M.、Litvinov, V. P.、Mortikov, V. Yu.、Rodinovskaya, L. A.、et. al.

  DOI：——

  日期：——